In the long and frequently litigious history of the America’s Cup, no city has been at the centre of more drama than San Diego. The city hosted two consecutive Cups — 1988 and 1992 — and both rewrote the rules of the sport. One ended in the New York Supreme Court. The other produced the IACC class that would govern the Cup for the next fifteen years and generate some of the finest match racing in the event’s history.
Understanding what happened in San Diego, and why it mattered, explains much of how modern grand-prix sailing got to where it is today.
How San Diego got the Cup
The story begins in Newport, Rhode Island, in 1983 — the year Australia II, with her radical winged keel, ended 132 years of American dominance in the America’s Cup. The loss sent shockwaves through the American sailing establishment and produced a determination to win the trophy back.
Dennis Conner — the skipper who had lost the Cup on Australia II’s last leg — spent four years and $15 million preparing for the 1987 challenger series in Fremantle. His boat, Stars & Stripes, was optimised for Fremantle’s notorious 25–35-knot afternoon breeze (the Fremantle Doctor). The 1987 Cup was sailed in exactly those conditions, and Stars & Stripes demolished the competition, winning back the trophy 4–0 against Kookaburra III.
Conner brought the Cup back to his home city. San Diego, for the first time in the trophy’s history, would be the Cup venue — and San Diego Yacht Club, Conner’s home club, would be the defender.
1988: the mismatch that went to court
The 1987 rules specified that challengers must notify the defender of their intent to race within six months of the Cup’s completion. A challenger from New Zealand, Mercury Bay Boating Club, did exactly that — but filed a challenge under the original 1887 Deed of Gift, the ancient founding document that governed the Cup before a more modern racing agreement was established.
The Deed of Gift challenge meant the defender could choose the boat type. New Zealand chose a 90-foot monohull — enormous by the standards of the 12-Metre class that had been used since 1958. The boat was built in secret. San Diego Yacht Club, facing a boat with a 90-ft waterline, responded by building a catamaran.
The catamaran, Stars & Stripes ‘88, was a 60-ft wing-sail cat — a completely different type of vessel from anything seen in America’s Cup competition. New Zealand protested. San Diego argued the Deed allowed any type of vessel. The New York courts initially sided with New Zealand; appeals sided with San Diego. The races were sailed in September 1988 in San Diego Bay.
The result was not close. A modern performance catamaran against a 90-ft monohull is not a race; it is a demonstration of physics. Stars & Stripes won both races by margins of 18 and 21 minutes. New Zealand’s skipper David Barnes described the experience as racing a sports car against a bicycle.
New Zealand challenged the result in court. After years of litigation, the New York Court of Appeals ultimately ruled in San Diego’s favour in 1990 — the catamaran victory stood. But both camps agreed that the Deed of Gift challenge system was broken and that a new class rule was needed before the 1992 Cup.
The birth of the IACC
The International America’s Cup Class (IACC) was the result. Developed collaboratively between 1988 and 1991 by the major Cup syndicates, the IACC rule specified a boat of approximately 75 ft overall with a 110-ft carbon mast, a 25-ton displacement, and a complex measurement formula that balanced speed against stability and cost. The formula was designed to produce fast, evenly matched boats raced in conditions consistent with San Diego Bay — 8–20 knots of breeze, moderate swell.
The IACC rule was a working landmark in yacht-design regulation. Rather than specifying dimensions directly, it used a velocity-prediction program to establish a rating — boats of different proportions could be built, but the formula penalised extremes. Within those bounds, designers were free to innovate. The result was fifteen years of intense, productive design competition that produced some of the most sophisticated one-design-adjacent racing yachts ever built.
The first IACC boats were built for the 1992 Cup in San Diego. Seven syndicates entered. Construction alone represented an estimated $300 million in total investment across all programmes.
1992: Il Moro di Venezia and the Italian challenge
The 1992 Cup is remembered less for controversy than for racing quality. The Italian syndicate, Raul Gardini’s Il Moro di Venezia, produced a fast, well-sailed challenger that gave the US defenders genuine difficulty through the Louis Vuitton Cup challenger series.
America3, the defender skippered by Bill Koch, was a programme built around a controversial decision: a female sailing team, the Mighty Mary, was integrated into the training structure. Koch’s campaign was one of the most scientifically managed in Cup history up to that point — wind-tunnel testing, computational fluid dynamics, a systematic approach to performance optimisation that foreshadowed what would become standard practice.
The Cup itself, sailed on San Diego Bay in May 1992, went four races to one for America3. Il Moro di Venezia was competitive throughout, particularly upwind where the Italian boat’s design was superior. Koch’s team responded with tactical and strategic excellence that more than compensated.
The racing took place on a course set in the outer bay and ocean south of Point Loma — the same waters visible from Shelter Island today. The afternoon breeze was consistent, the conditions close to ideal, and the match racing, while not the closest in Cup history, showcased what the new IACC class was capable of.
What San Diego left behind
Two Cup campaigns defined the working terms on which the modern America’s Cup is contested.
The Deed of Gift limitation was exposed definitively in 1988. The subsequent agreement between competing nations created the protocol system — a document negotiated before each Cup that governs the class, the venue, the format, and the dispute-resolution process. Every America’s Cup since 1992 has been governed by a protocol rather than the bare Deed of Gift. San Diego’s courtroom drama made that change necessary.
The IACC class governed the Cup through 1992, 1995 (San Diego again, won by New Zealand’s Team New Zealand), 2000, 2003, and 2007. The 2007 Valencia Cup, sailed between Alinghi and Emirates Team New Zealand, produced what many consider the finest match racing in Cup history — two evenly matched IACC boats on a tight course in consistent Mediterranean conditions. The IACC era lasted 15 years and is still considered the working golden age of America’s Cup monohull racing.
The catamaran question remained unresolved by 1988 but came back around: the 34th and 35th Cups, sailed in 2013 and 2017, used multihulls. The 36th and 37th Cups returned to monohulls — but foiling AC75s, not IACC boats. The question of what the optimal America’s Cup boat looks like remains genuinely contested.
The boats that still sail
Several IACC yachts from the San Diego era remain actively sailing from Shelter Island, operated as charter vessels by a small group of operators who have maintained them in sailing condition. This is unusual. Most retired Cup boats from this era are in museums or private collections; the capital and expertise required to keep an IACC boat seaworthy is substantial.
The boats that guests can crew on today are the direct descendants of the 1992 Cup campaign — the same class, similar vintage, maintained by teams who understand their history. Grinding the winches on one of these boats in San Diego Bay, with Point Loma visible to the west and the Hotel del Coronado across the water, is as close as most sailors will get to the working technical reality of what Cup racing felt like in the IACC era.
It is not a recreation. It is the actual thing, sailed in the actual place, on the water where it happened. That combination is genuinely rare in working sport.
How to experience it
San Diego’s America’s Cup charter operators run two-hour racing experiences from Shelter Island year-round, weather permitting. Shared charters typically accommodate up to 16 guests at $150–200 per person; private charters of the full boat are available for groups. The afternoon window — when San Diego’s thermal breeze is at its most reliable — is the standard departure time.
For the working sailing-history-curious customer, the combination of the physical experience and the historical context makes this one of the more unusual things to do in American sport. The boats raced in competition for the sport’s oldest trophy. They sail on the water where they did it. They remain fast enough, even now, to remind a guest why they were worth building in the first place.
Related: Sail an America’s Cup Yacht in San Diego · San Diego Bay Cruising Guide · Sailing San Diego Bay · Southern California Cruising Guide